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Whitey Bulger
AP Photo/Charles Krupa
Bulger was a Hollywood favorite.
DEARLY DEPARTED

How the stranger-than-fiction story of Whitey Bulger has been told on screen

By Adam Epstein

James “Whitey” Bulger is dead, but the notorious crime boss will live on in the popular imagination and on the screen.

Bulger, 89, was found dead in a West Virginia prison today, according to various reports. He was serving two life sentences for 11 murders, and had just been transferred from a facility in Florida to the high-security prison in West Virginia this past week. The New York Times reports that he was beaten to death by two mob-affiliated inmates, citing two unnamed prison officials.

It’s an ignominious end for the Irish-American gangster, whose wild, stranger-than-fiction life before and after he went on the lam in 1994 and became one of America’s most wanted criminals has been written about extensively (including in a biography by two Boston Globe reporters), and depicted on screen several times. While many American “mob boss” characters today are based loosely on Bulger—or are composites of famous American mobsters, including Bulger—two major Hollywood productions and a documentary feature Bulger prominently:

Black Mass

The most recent—and direct—adaptation of Bulger’s story is Black Mass, the 2015 biopic starring Johnny Depp in a role that earned the actor a Screen Actors Guild award nomination. Reviewers said the role was one of the best in many years for Depp, who donned a fake receding hairline, bad teeth, and bright blue contacts to become the infamous mobster.

The film picks up in 1975, when Bulger was already the head of the powerful Winter Hill Gang crime organization in and around Boston. Joel Edgerton plays John Connolly, an FBI agent who grew up with Bulger and eventually became his handler as an informant. Connolly was effectively handled instead by Bulger, becoming his eyes and ears inside the bureau and helping the mob boss undermine rival gangs, as well as covering up murders he was involved in or ordered. The real-life Connolly is currently serving out the remainder of a 40-year sentence issued in 2008, after he was convicted of second degree murder.

Depp reportedly watched FBI surveillance footage of Bulger and spoke to his former attorney to nail the man’s mannerisms. (The film itself received middling reviews from critics, but Depp’s performance was praised.) Black Mass can be viewed on Amazon, YouTube, or iTunes.

The Departed

Martin Scorsese’s 2006 crime film, which won the Oscar for best picture the following year, was loosely based on Bulger and his Winter Hill Gang. The film legend Jack Nicholson plays Frank Costello, the leader of a crime syndicate in Boston, while Matt Damon plays Colin Sullivan—Costello’s mole inside the Massachusetts State Police, who’s clearly inspired by Connolly and his relationship to Bulger.

The Departed was originally an adaptation of the 2002 Hong Kong thriller Infernal Affairs, but Scorsese said Nicholson wanted an extra element to make the story more immediate. That’s when screenwriter William Monahan came up with the idea to base Nicholson’s and Damon’s characters on Bulger and Connolly, respectively. Leonardo DiCaprio plays a young state trooper who goes undercover in Costello’s organization as he races to discover Costello’s mole before Costello realizes he’s a cop.

When the film was released, Bulger was still on the run. He was reportedly seen watching The Departed in a movie theater in San Diego that year, a tipster told the Boston Globe. The Departed can be viewed on Amazon, YouTube, or iTunes.

Whitey: United States of America v. James J. Bulger

Three years after Bulger was captured in 2011, and a few months following his sentencing of two consecutive life terms in prison, CNN Films co-produced this documentary about the mobster’s life and various trials. It premiered at the 2014 Sundance Film Festival and received solid reviews from critics, though they noted that Bulger’s life of crime was perhaps too sprawling for any one documentary to cover completely.

Whitey: United States of America v. James J. Bulger can be viewed on Hulu and Amazon.

Other roles inspired by Bulger

A number of major television characters are based in part on Bulger. These include:

  • “Sully Sullivan” in the Showtime crime drama Ray Donovan (played by James Woods)
  • “Paddy Doyle” in TNT series Rizzoli & Isles (played by John Doman)
  • “Raymond ‘Red’ Reddington” in NBC crime series The Blacklist (played by James Spader)

The film that never was

Fellow Bostonians Matt Damon and Ben Affleck were reportedly working on a film with Warner Bros, scripted by Terence Winter (the creator and writer of Boardwalk Empire), but it did not move forward after Black Mass was released in 2015.

“We had a very different take on it,” Damon told the Hollywood Reporter in 2015. He said that he and Affleck had received a letter from a South Boston author that made them rethink the project. “It was a really moving letter that basically said: ‘Don’t glorify this man any more. Please stop.’ And this is to take nothing away from Black Mass. I hear the movie’s great. But Ben and I agreed with the guy who’d written us. And so we came up with this idea of doing it more like an anti-gangster movie. Make it look like what it was: something grotesque.”